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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2629
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COC1=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI
Molecular Formula C16H12O6
Molecular Weight 300.2629
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

CNS Activity

Originator

Oesterle, O.A.|Wander, G.
1
Sources: DOI: 10.1002/hlca.19250080179

Approval Year

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 140.0 nM [IC50]
Inhibitor
8297
 2.4 µM [IC50]
Inhibitor
8297
 29.0 nM [IC50]
Agonist
2678
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003 Sep 9
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
The efflux of flavonoids morin, isorhamnetin-3-O-rutinoside and diosmetin-7-O-beta-D-xylopyranosyl-(1-6) -beta-D-glucopyranoside in the human intestinal cell line caco-2.
2006 Aug
A new flavone glycoside from the fruits of Luffa cylindrica.
2007 Dec
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
2007 Feb
Two new flavonoids from Origanum vulgare.
2008
Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.
2008 Dec 24
New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry.
2008 Jun
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
2008 Mar 15
[Studies on chemical components of Lobelia chinensis].
2009 Feb
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.
2009 Feb
Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.
2009 Feb
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009 Feb
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.
2009 Jan 8
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.
2009 Jul
Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.
2009 Jun
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
2009 Jun 16
The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece-Crete indicates a new commercial source of hesperidin.
2009 Mar
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
2009 Mar 25
[Chemical constituents of Galium verum].
2009 Nov
[Studies on flavones from Flos Chrysanthemi Indici].
2009 Oct
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.
2009 Sep
[Chemical constituents of Lobelia chinensis].
2009 Sep
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.
2010
Flavonoids and antioxidant activity of Rosa agrestis leaves.
2010 Apr
Beta-glucuronidase from Helix pomatia origin is not suitable for diosmetin analysis.
2010 Dec 1
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.
2010 Jan 28
Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts.
2010 Jul
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study.
2010 Mar 11
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
2011 May 1
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Patents

JP2007223914A
1
JP2010521566A
4
JP2011505817A
2
JP4370072B2
48

Sample Use Guides

In Vivo Use Guide
Mice: 50mg /kg/every other day for 6 weeks
Route of Administration: Intraperitoneal
In Vitro Use Guide
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:33:37 GMT 2023
Edited
by admin
on Fri Dec 15 17:33:37 GMT 2023
Record UNII
TWZ37241OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSMETIN
INCI   MI   WHO-DD  
INCI  
Official Name English
4'-METHYLLUTEOLIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE
Systematic Name English
DIOSMETIN [INCI]
Common Name English
DIOSMETIN [MI]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE
Systematic Name English
DIOSMETINE
Common Name English
LUTEOLIN-4'-METHYL ETHER
Common Name English
CYANIDENON-4'-METHYL ETHER 1479
Common Name English
DIOSMETOL
Common Name English
Diosmetin [WHO-DD]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
Classification Tree Code System Code
DSLD 4156 (Number of products:7)
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
HSDB
8101
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID80199966
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
DAILYMED
TWZ37241OT
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
SMS_ID
100000128590
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
PUBCHEM
5281612
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
CHEBI
4630
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
RXCUI
1314347
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
DRUG CENTRAL
4601
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
MERCK INDEX
m4594
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY Merck Index
MESH
C039602
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
DRUG BANK
DB11259
Created by admin on Fri Dec 15 17:33:37 GMT 2023 , Edited by admin on Fri Dec 15 17:33:37 GMT 2023
PRIMARY
Related Record Type Details
AGATHOSMA BETULINA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of Diosmin
PARENT -> IMPURITY
NMT 3%
USP
Related Record Type Details
Structure of DIOSMETIN
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
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